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含羟基苯甲酸甲酯的顺、反丁烯二酸酯类化合物的合成及抑菌活性
引用本文:马延龙,周如金,曾兴业,邱松山,聂丽君.含羟基苯甲酸甲酯的顺、反丁烯二酸酯类化合物的合成及抑菌活性[J].食品科学,2014,35(17):118-122.
作者姓名:马延龙  周如金  曾兴业  邱松山  聂丽君
作者单位:1.江苏科技大学生物与化学工程学院,江苏 镇江 212003;2.广东石油化工学院化学工程学院,广东 茂名 525000
基金项目:广东省教育部产学研结合项目(2009B090300134);广东省高等学校高层次人才项目
摘    要:以顺、反丁烯二酸单酯和o,m,p-羟基苯甲酸甲酯为起始原料合成了6 种新型的含羟基苯甲酸甲酯单元的顺、反丁烯二酸酯类化合物,目的在于发现新的具有抑制食品相关细菌和真菌生长能力的生物活性分子。产物结构经液相色谱-质谱联用(liquid chromatography mass spectrometer,LC-MS)、核磁共振(nuclear magneticresonance,NMR)表征和元素分析。体外抑菌活性实验结果表明,所有合成的化合物对8 种供试菌有着较好的抑菌效果,化合物4a的抑菌活性最强(最低抑菌浓度(minimum inhibitory concentration,MIC)≤75 μg/mL),化合物4a对酿酒酵母、黄曲霉和产黄青霉的MIC分别为25、37.5、37.5 μg/mL。

关 键 词:顺、反丁烯二酸酯类化合物  合成  抑菌活性  

Synthesis and Antimicrobial Activity of Novel cis/trans-But-2-Enedioic Acid Esters Containing a Hydroxybenzoic Acid Methyl Ester Moiety
MA Yan-long,ZHOU Ru-jin,ZENG Xing-ye,QIU Song-shan,NIE Li-jun.Synthesis and Antimicrobial Activity of Novel cis/trans-But-2-Enedioic Acid Esters Containing a Hydroxybenzoic Acid Methyl Ester Moiety[J].Food Science,2014,35(17):118-122.
Authors:MA Yan-long  ZHOU Ru-jin  ZENG Xing-ye  QIU Song-shan  NIE Li-jun
Affiliation:1. School of Biological and Chemical Engineering, Jiangsu University of Science and Technology, Zhenjiang 212003, China; 2. College of Chemical Engineering, Guangdong University of Petrochemical Technology, Maoming 525000, China
Abstract:Six novel cis/trans-but-2-enedioic acid esters containing a hydroxybenzoic acid methyl ester moiety were
synthesized as potential food preservatives, aiming to discover the new bioactive molecules that can kill food-related
bacteria and fungi, and their structures were characterized by liquid chromatography-mass spectrometry (LC-MS), nuclear
magnetic resonance (NMR) and elemental analysis. The antimicrobial activity assays in vitro showed that these compounds
had strong bioactivity against all eight microorganisms tested. Among the most promising antibacterial and antifungal
compounds, 4-(methoxycarbonyl) phenyl methyl fumarate (4a) showed the best antimicrobial activity, and it was effective
against S. cerevisiae, A. flavus and P. chrysogenum with minimal inhibition concentration (MIC) of 25, 37.5 and 37.5 μg/mL,
respectively.
Keywords:cis/trans-but-2-enedioic acid esters  synthesis  antimicrobial activity  
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